Hydrogenated diglycidyl ethers of bipheny-4,4′-diol

Details Hydrogenated diglycidyl ethers of bipheny-4,4′-diol Hydrogenated diglycidyl ethers of bipheny-4,4′-diol

1999-05-28

2001-05-15

Sellers, Robert E. L. (Department: 1712)

Synthetic resins or natural rubbers -- part of the class 520 ser

Synthetic resins

Mixing of two or more solid polymers; mixing of solid...

C528S087000, C528S098000

Reexamination Certificate

active

06232411

ABSTRACT:

FIELD OF THE INVENTION
The present invention relates to a novel epoxy compound and a method of preparing the same. More particularly, the present invention relates to a novel epoxy compound that provides excellent workability because the compound is liquid or a solid having a low melting point, and can be used as resins for encapsulation of semiconductors, laminates, coatings, adhesives, casting materials and electrical insulation materials.
BACKGROUND OF THE INVENTION
Epoxy resins have been employed in a variety of fields because of their excellent properties such as heat resistance, adhesion, water resistance, mechanical strength and electrical properties. Especially in electrical and electronic fields, epoxy resins have found widespread use as electrical insulation castings, laminating materials and materials for encapsulation. However, in recent years, with the miniaturization, high precision and high performance of electrical and electronic components, there has been a demand for molding properties, high moisture resistance and high electrical properties of epoxy resins to be used.
For example, recently, LSI packaging is showing the trend of high density and thin shape, with the development of portable devices such as IC cards, LCDs, portable telephones and note-type personal computers, and is changing the process thereof from the conventional transfer-molding packaging to so-called COB (chip-on-board) or TAB processes in which bare chips are mounted and are encapsulated with liquid encapsulating materials. The epoxy resins that are made from bisphenol A or bisphenol F are main streams of the conventional epoxy resins for liquid encapsulation. However, there has been a demand for the improvement of reliability of liquid encapsulating materials because these resins have poor moisture resistance and poor heat resistance.
A method has been proposed in which biphenyl type crystalline epoxy resins having low stress, low moisture absorption, and excellent crack-resistance in soldering, which are used in large quantities as LSI-packaging materials for transfer molding use, or to make the resins have a low melting point, is liquefied or subjected to have a low melting point (confer Japanese Unexamined Patent Publication No. Sho 07-62060). However, in this method, since considerably large amounts of phenol compounds or compounds having carboxyl groups are subjected to a reaction with biphenyl type epoxy resins, obtained epoxy resins do not have satisfactory curing characteristics and cured resins therefrom do not have satisfactory heat resistance.
SUMMARY OF THE INVENTION
The present invention has been made to solve the above-mentioned problem, and an object of the present invention is to provide a novel liquid or low-melting-solid epoxy compound having low melt viscosity which conventional epoxy compounds do not have and being capable of giving cured resins with a good balance between moisture resistance and heat resistance.
The present invention relates to a novel epoxy compound that is obtained by hydrogenation of a biphenyl-type aromatic epoxy compound, and to a method of preparing the same. The present invention comprises the following aspects of the invention.
(1) An epoxy compound represented by general formula (1);
wherein R
1
to R
4
each represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms; n represents an integer of 0 to 6 and Z
1
and Z
2
each represent general formula (2) or (3);
wherein R
5
to R
8
each represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.
(2) A method of preparing an epoxy compound represented by general formula (1);
wherein R
1
to R
4
each represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms; n represents an integer of 0 to 6 and Z
1
and Z
2
each represent general formula (2) or (3);
wherein R
5
to R
8
each represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, which is characterized by hydrogenation of an aromatic epoxy compound represented by general formula (4);
wherein R
1
to R
8
each represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms and n represents an integer of 0 to 6.
(3) A method of preparing an epoxy compound as described in the item (2), characterized in that the hydrogenation is a reaction preparing an epoxy compound represented by general formula (1) by hydrogenating the aromatic epoxy compound represented by general formula (4) dissolved in an ether-based solvent under pressure in the presence of a catalyst in which rhodium or ruthenium is carried on a graphite.
(4) A method of preparing an epoxy compound as described in the item (2) or (3), characterized in that the hydrogenation is a reaction hydrogenating the aromatic epoxy compound represented by general formula (4) to such an extent that a hydrogenation rate of aromatic rings of the aromatic epoxy compound becomes 10 to 100%.
(5) A method of preparing an epoxy compound as described in any one of the items (2) to (4), characterized in that the hydrogenation is a reaction hydrogenating the aromatic epoxy compound of general formula (4) to such an extent that a hydrogenation rate of aromatic rings of the aromatic epoxy compound becomes 20 to 90%.
(6) A method of preparing an epoxy compound as described in any one of the items (2) to (5), characterized in that an aromatic epoxy compound represented by general formula (4) is an aromatic epoxy compound represented by general formula (4); wherein R
1
, R
2
, R
7
and R
8
each represent a hydrogen atom or a methyl group; R
3
, R
4
, R
5
and R
6
each represent a hydrogen atom and n represents an integer of 0 to 3.
(7) A curing composition characterized by containing one or two or more of epoxy compounds represented by general formula (1) in the item (1) and curing agents for epoxy compounds.


REFERENCES:
patent: 1243045 (1988-10-01), None

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